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The Sleepy Hollow Half Marathon – The Northeast’s First Destination Race of the Season

by Jay Flemma,
special to Slave to the Traffic Light Magazin


Dear Runner’s World:

Grab a pin, and take out your running map. It’s time to permanently add a new destination race to the annual calendar.

Sleepy Hollow, cozily nestled between the frowning, dark hardwoods of the Rockefeller State Forest on the one side, and the rocky façade of the Palisades looming over the Hudson River on the other, comes alive in all its Colonial charm and grandeur every March for a half marathon that Mid-Atlantic runners are calling their Annual Running Rite of Spring.

Hosted by one of the most convivial running clubs in America, the Rivertown Runners, the Sleepy Hollow Half isn’t just a road race; it’s a trip 200 years back in time to when author Washington Irving made the town an indelible part of American literature and popular culture with his timeless classic The Legend of Sleepy Hollow. It’s inspiring to see how the town both preserves and promotes its precious heritage; the Headless Horseman is everywhere you look, and the Half Marathon is no exception.

Better still, for northerners still thawing out from winter’s freeze it’s also the perfect way to open the competitive racing season. Whether you’re an expert runner prepping for April’s Boston Marathon, a newbie looking for an unforgettable setting for that first half, or just any runner begging to get out of the damn snow, Sleepy Hollow is the right race, in the right place, at the right time.

The race course reflects the town’s forbidding reputation – both figuratively and literally. Sleepy is tough because it’s hilly: boasting over 1,300 feet of elevation change, with a net uphill gain of 300 feet, (800 up, 500 down).

“Uphill, then uphill, then uphill some more, then a BIG uphill and, of course, the big uphill finish,” was the way one irreverent wag described it, and there’s some truth to what he says, and some mischievous hyperbole too. Sleepy is not simply “hard for hard’s sake” – the route incorporates some of the most character-rich landmarks in the area. But to enjoy them, you have to climb some hills.

The race starts in the heart of the town before immediately ascending into the Rockefeller State Forest – the same haunted woods where hapless Ichabod Crane got whacked by the Headless Horseman. It’s a formidable beginning, traversing hurly-burly switchbacks with the forest looming gloomily over you. But at varying points in the first five miles, the course will suddenly spill out into a verdant glade, a clearing, or a small lake, and angelic shafts of light, finally freed from the tyranny of the trees, will burnish all the landscape in dazzling gold.

It’s one of those moments you came here for.

Runners then emerge onto Route 117 for a two mile stretch before turning to the majestic Hudson River, with the stone faces of the Palisades towering over the placid waters. On a sunny day, sailboats and other craft will navigate their way serenely across as you run by, and dappled sunshine will reflect off the water in a blaze of glory.

Those are some of the other moments you came here for.

The last half of the race will follow the river – one breathtaking view after another – while also winding through the stately manors and quaint homes, before one last turn into Kingsland Point Park, and a look at the town lighthouse.

Ah yes, the lighthouse, which you’re not allowed to make fun of, but everyone does anyway. Size matters, yet Sleepy Hollow denizens have not discovered Architectural Viagra for their vertically-challenged lighthouse. How short is it? I think I saw Hobbits frolicking under it during last year’s race, or was it Oompa-Loompas? I can never tell the difference…


Anyway, after giving Frodo Baggins a high-five, you make a final turn back into town and the 175-yard long, 300-foot high ascent to the finish line, your medal, and more panoramic views of the Hudson, one of the best settings for a post-race photo anywhere in America.

Sleepy is not a PR course, but it is indispensable. Between the town’s iconic contribution to world literature, its venerable Colonial history, and the all but unparalleled natural setting, it’s a must-run race. Don’t let the hills scare you off – many of the best destination half marathons are also particularly hilly, so Sleepy is good prep. Besides, there’s a saying about people who skip a great destination race just because someone else told them it’s a tough and hilly: YA SNOOZE, YA LOSE!


There’s also one other important reason to run Sleepy Hollow: the weather. Sleepy is the first reasonable-weather long run in the Northeast. As I write this on March 3, the entire northeast is digging out from another “bombogenesis.” Something called Winter Storm Riley sat his frozen butt right on top of upstate New York and farted 24 inches of snow all over us (and 38 inches in Albany!) with winds strong enough to knock down utility poles, and a white-out that left tractor-trailers jack-knifed in ditches. This sort of thing goes on for close to five months along I-90 and I-87.

Now try training for half marathons in it! It’s sheer murder.

By the time March rolls around, we’re stir crazy. So Sleepy Hollow is perfect: winter’s somber chill has finally faded, and we need a running springboard to catapult us into the season.

Cue the Rivertown Runners, as amiable, energetic, creative, and close-knit as you could ask for in a running group. Every week has at least three runs, but also a fun event too to promote camaraderie. Visiting runners from clubs all across the country come to visit and practice with them even when it’s not the week of the half marathon or their wildly popular Halloween 10K, where they actually dress up someone in a Headless Horseman outfit and have him chase you around the woods. No head – of course not – but he’s got a pumpkin, and it’s in flames.

Sleepy Hollow is Americana, history, literature, all in a breathtaking setting, and the thought of the Sleepy Hollow Half Marathon warms a northeastern runner’s heart all winter long, the perfect fuse to light the season’s running fireworks. In fact, you can fill out your early spring running calendar like this: Sleepy Half late March, Boston in Mid April, and then either Pittsburgh or Cincinnati first weekend of May. That’s three world class races in six weeks in four of the country’s most interesting, vibrant, and historic cities. And if that doesn’t grab ya, well, come for the FREE BEER! That never gets old.

What: Sleepy Hollow Half Marathon, www.rivertownrunners.org
When: Saturday March 24, 9:30 start
Where: Sleepy Hollow, New York
Who: The Rivertown Runners


Size: This year 720 runners participated, but it can fit many more.

Difficulty for that length: 5.5 – 6 out of 7 – Tough but fair, you don’t get much of a break going downhill due to the steep descents.

Natural Setting: 5.5 – 6 out of 7

Weather: 4.5 – 5 out of 7 – IN the northeast, March has come in like a lion, and goes out like one of Danaerys Targaryen’s dragons. But barring a freak Winter Storm, you’ll like be running 55 degree temperatures, a welcome respite after a northeast winter where you’re running in 4-degrees temperatures, minus-10 with the wind chill.

Value: 6 out of 7 – At a fraction of the cost of other NYC-area races, it’s easily the best bargain. Plus you get a free Tech shirt, sometimes featuring the Horseman.

After Party: 5 out of 7 – The race ends right in the village, so the bar scene afterwards is high energy.

Fun: 7 out of 7 – You can tell a truly great race because its whole experience is greater than the sum of its parts. That’s especially true at Sleepy Hollow.